80099-85-0

Upstream product

• 109-09-1 2-chloropyridine 
• 122-01-0 4-chloro-benzoyl chloride 
• 49609-84-9 2-Chloronicotinoyl chloride 
• 108-90-7 chlorobenzene 
• 2942-59-8 2-chloronicotinic acid 
• 488149-34-4 2-chloro-N-methoxy-N-methyl-pyridine-3-carboxamide 
• 873-77-8 (4-chlorphenyl)magnesium bromide 

Downstream Products

• 1186316-75-5 VER-156085 
• 1186316-73-3 VER-156084 
• 1186316-76-6 VER-24052 
• 1357306-02-5 C₁₆H₁₃Cl₃N₂O₂ 
• 791119-12-5 1-benzhydyryl-3-(4-chlorophenyl-2-chloropyrid-3-ylmethoxy)azetidine 
• 1357305-47-5 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}pyrrolidin-1-ylmethanone 
• 1357305-50-0 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}morpholin-4-ylmethanone 
• 1357305-51-1 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}(2-methylpiperidin-1-yl)methanone 
• 1357305-52-2 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}(3-methylpiperidin-1-yl)methanone 
• 1357305-53-3 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}(4-methylpiperidin-1-yl)methanone 
• 1357305-54-4 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}(4-methylpiperazin-1-yl)methanone 
• 1357305-55-5 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}(4-benzylpiperidin-1-yl)methanone 
• 1357305-56-6 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}(4-benzylpiperazin-1-yl)methanone 
• 1357305-57-7 {3-[(4-chlorophenyl)(2-chloropyridin-3-yl)methoxy]azetidin-1-yl}(3-hydroxypyrrolidin-1-yl)methanone 

Relevant academic research and scientific papers

Difluorocarbene-triggered cyclization: Synthesis of (hetero)arene-fused 2,2-difluoro-2,3-dihydrothiophenes

An efficient method for the synthesis of (hetero)arene-fused 2,2-difluoro-2,3-dihydrothiophene derivatives using readily available sodium chlorodifluoroacetate (ClCF2CO2Na) has been developed. This transformation is achieved through a combination of a thi

Azine and Diazine Functionalization Using 2,2,6,6-Tetramethylpiperidino-Based Lithium-Metal Combinations: Application to the Synthesis of 5,9-Disubstituted Pyrido[3′,2′:4,5]pyrrolo[1,2- c ]pyrimidines

The synthesis of triaryl methanols was investigated by reacting different 4-metalated 2-substituted pyrimidines with diaryl ketones, the latter being generated by deprotocupration-aroylation of azine and diazine substrates. Cyclization of the triaryl meth

Synthesis of azafluorenones and related compounds using deprotocupration-aroylation followed by intramolecular direct arylation

The efficiency of the deprotocupration-aroylation of 2-chloropyridine using lithiocuprates prepared from CuX (X=Cl, Br) and LiTMP (TMP=2,2,6,6- tetramethylpiperidido, 2 equiv) was investigated. CuCl was identified as a more suitable copper source than CuBr for this purpose. Different diaryl ketones bearing a halogen at the 2 position of one of the aryl groups were synthesized in this way from azines and thiophenes. These were then involved in palladium-catalyzed ring closure: substrates underwent expected CH-activation-type arylation to afford fluorenone-type compounds, and were also subjected to cyclization reactions leading to xanthones, notably in the presence of oxygen-containing substituents or reagents.

Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity

We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats.

Deprotonative metalation of chloro- and bromopyridines using amido-based bimetallic species and regioselectivity-computed CH acidity relationships

A series of chloro- and bromopyridines have been deprotometalated by using a range of 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal combinations. Whereas lithium-zinc and lithium-cadmium bases afforded different mono- and diiodides after subsequent interception with iodine, complete regioselectivities were observed with the corresponding lithium-copper combination, as demonstrated by subsequent trapping with benzoyl chlorides. The obtained selectivities have been discussed in light of the CH acidities of the substrates, determined both in the gas phase and as a solution in THF by using the DFT B3LYP method.

Fatty acid amide hydrolase inhibitors. 2. Novel synthesis of sterically hindered azabenzhydryl ethers and an improved synthesis of VER-156084

We report an improved synthesis of the fatty acid amide hydrolase (FAAH) inhibitor VER-156084. The key step is a novel, environmentally benign etherification to form an unusual, highly hindered azabenzhydryl ether. The method is applied to a variety of pr

Fatty acid amide hydrolase inhibitors. Surprising selectivity of chiral azetidine ureas

We report the discovery of a novel, chiral azetidine urea inhibitor of Fatty Acid Amide Hydrolase (FAAH,) and describe the surprising species selectivity of VER-156084 versus rat and human FAAH and also hCB1.

NEW COMPOUNDS

The present invention relates to new mGluR1 and mGluR5 receptor subtype preferring ligands of formula (I); wherein Y represents a subtituent selected from hydrogen, methyl, fluoro, chloro, bromo, methoxy; Z is hydrogen or methyl; R is an optionally substi

THIENOPYRIDINE DERIVATIVES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS

The present invention relates to new mGluRl and niGluR5 receptor subtype preferring ligands of formula (I): wherein X represents a group selected from (CH2)n, CH=CH, NH, N(CH3), NHCH2, N(CH3)CH2, O, OCH2, CH2COO, NHCH2COO; n is an integer of O to 2; Y represents a subtituent selected from H, CH3, F, Cl, Br; Z is H or CH3; R is alkyl, cycloalkyl, an optionally substituted phenyl or an optionally substituted heteroaryl, and/or geometric isomers and/or salts and/or hydrates and/or solvates thereof, to the processes for producing the same, to pharmaceutical compositions containing the same and to their use in therapy and/or prevention of pathological conditions which require the modulation of mGluRl mGluR5 receptors such as neurological disorders, psychiatric disorders, acute and chronic pain and neuromuscular dysfunctions of the lower urinary tract.